NO321606B1 - Pyrrolderivater og medisinsk sammensetning - Google Patents

Pyrrolderivater og medisinsk sammensetning Download PDF

Info

Publication number: NO321606B1
Authority: NO; Norway
Prior art keywords: substituted; hydrogen; cyano; compound; pollakiuria
Prior art date: 1995-06-07

Application number

NO19975666A

Other languages

English (en)

Norwegian (no)

Other versions

NO975666D0 (no

NO975666L (no

Inventor

Masami Tsuda

Mitsushi Tanaka

Ayatsugu Nakamura

Original Assignee

Nippon Shinyaku Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1995-06-07

Filing date

1997-12-05

Publication date

2006-06-12

1997-12-05 Application filed by Nippon Shinyaku Co Ltd filed Critical Nippon Shinyaku Co Ltd

1997-12-05 Publication of NO975666D0 publication Critical patent/NO975666D0/no

1998-02-09 Publication of NO975666L publication Critical patent/NO975666L/no

2006-06-12 Publication of NO321606B1 publication Critical patent/NO321606B1/no

Links

150000003233 pyrroles Chemical class 0.000 title claims abstract description 8
239000000203 mixture Substances 0.000 title description 25
206010036018 Pollakiuria Diseases 0.000 claims abstract description 13
206010046543 Urinary incontinence Diseases 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
239000012453 solvate Substances 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
239000004480 active ingredient Substances 0.000 claims abstract description 4
-1 monoalkylamino Chemical group 0.000 claims abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
239000003814 drug Substances 0.000 claims description 7
229940079593 drug Drugs 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract 2
125000003118 aryl group Chemical group 0.000 abstract 2
125000004466 alkoxycarbonylamino group Chemical group 0.000 abstract 1
125000002947 alkylene group Chemical group 0.000 abstract 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
125000004663 dialkyl amino group Chemical group 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 30
210000003932 urinary bladder Anatomy 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
239000013078 crystal Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
238000012360 testing method Methods 0.000 description 12
230000001965 increasing effect Effects 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 8
238000001816 cooling Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000003826 tablet Substances 0.000 description 6
238000009472 formulation Methods 0.000 description 5
238000000034 method Methods 0.000 description 5
230000027939 micturition Effects 0.000 description 5
229940126585 therapeutic drug Drugs 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
NUPLLTDVHPEUQM-UHFFFAOYSA-N 2-cyanoethanimidamide Chemical compound NC(=N)CC#N NUPLLTDVHPEUQM-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000003480 eluent Substances 0.000 description 3
UMXADXYSYVKRJV-UHFFFAOYSA-N ethyl 2-cyanoethanimidate;hydrochloride Chemical compound Cl.CCOC(=N)CC#N UMXADXYSYVKRJV-UHFFFAOYSA-N 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000006186 oral dosage form Substances 0.000 description 3
239000007935 oral tablet Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
KVDWOQGDMAEJLM-UHFFFAOYSA-N 2-amino-5-(2-fluorophenyl)-4-methyl-1h-pyrrole-3-carbonitrile Chemical compound N1C(N)=C(C#N)C(C)=C1C1=CC=CC=C1F KVDWOQGDMAEJLM-UHFFFAOYSA-N 0.000 description 2
NIJBZJPXHOOJAX-UHFFFAOYSA-N 3-amino-3-morpholin-4-ylprop-2-enenitrile Chemical compound N#CC=C(N)N1CCOCC1 NIJBZJPXHOOJAX-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
230000008602 contraction Effects 0.000 description 2
238000011967 cystometrography Methods 0.000 description 2
230000034994 death Effects 0.000 description 2
231100000517 death Toxicity 0.000 description 2
CJTDBBPQNDKTLR-UHFFFAOYSA-N ethyl 2-cyanoethanimidate Chemical compound CCOC(=N)CC#N CJTDBBPQNDKTLR-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000001802 infusion Methods 0.000 description 2
230000036724 intravesical pressure Effects 0.000 description 2
AWFWQFVIIBYOKY-UHFFFAOYSA-N n-[1-(2-fluorophenyl)-2-oxopropyl]acetamide Chemical compound CC(=O)NC(C(C)=O)C1=CC=CC=C1F AWFWQFVIIBYOKY-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
210000002700 urine Anatomy 0.000 description 2
GANCPBMQNGCZGP-UHFFFAOYSA-N 2-amino-4-methyl-5-pyridin-3-yl-1h-pyrrole-3-carbonitrile Chemical compound N1C(N)=C(C#N)C(C)=C1C1=CC=CN=C1 GANCPBMQNGCZGP-UHFFFAOYSA-N 0.000 description 1
VPZYXGVUQMJVDM-UHFFFAOYSA-N 2-amino-4-methyl-5-pyridin-3-yl-1h-pyrrole-3-carbonitrile;hydrochloride Chemical compound Cl.N#CC1=C(N)NC(C=2C=NC=CC=2)=C1C VPZYXGVUQMJVDM-UHFFFAOYSA-N 0.000 description 1
HHFALDMLTBZLLQ-UHFFFAOYSA-N 2-amino-5-(2,5-difluorophenyl)-4-methyl-1h-pyrrole-3-carbonitrile Chemical compound N1C(N)=C(C#N)C(C)=C1C1=CC(F)=CC=C1F HHFALDMLTBZLLQ-UHFFFAOYSA-N 0.000 description 1
CGNMJIBUVDGMIY-UHFFFAOYSA-N 2-azaniumyl-2-(2-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=CC=C1F CGNMJIBUVDGMIY-UHFFFAOYSA-N 0.000 description 1
RVYATSSPBCRXII-UHFFFAOYSA-N 2-bromo-1-(2,5-difluorophenyl)propan-1-one Chemical compound CC(Br)C(=O)C1=CC(F)=CC=C1F RVYATSSPBCRXII-UHFFFAOYSA-N 0.000 description 1
QKHHCXOSPQAQQI-UHFFFAOYSA-N 2-bromo-1-(4-fluorophenyl)propan-1-one Chemical compound CC(Br)C(=O)C1=CC=C(F)C=C1 QKHHCXOSPQAQQI-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
ROLNTHGKCIIJBN-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-methyl-2-morpholin-4-yl-1h-pyrrole-3-carbonitrile Chemical compound N#CC=1C(C)=C(C=2C=CC(F)=CC=2)NC=1N1CCOCC1 ROLNTHGKCIIJBN-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
XIQVNETUBQGFHX-UHFFFAOYSA-N Ditropan Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC#CCN(CC)CC)C1CCCCC1 XIQVNETUBQGFHX-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241000282412 Homo Species 0.000 description 1
241000282414 Homo sapiens Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
QPCVHQBVMYCJOM-UHFFFAOYSA-N Propiverine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCC)C(=O)OC1CCN(C)CC1 QPCVHQBVMYCJOM-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
230000003187 abdominal effect Effects 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
238000011047 acute toxicity test Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
230000037396 body weight Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
210000001198 duodenum Anatomy 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229960000855 flavoxate Drugs 0.000 description 1
SPIUTQOUKAMGCX-UHFFFAOYSA-N flavoxate Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OCCN1CCCCC1 SPIUTQOUKAMGCX-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000003305 oral gavage Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229960005434 oxybutynin Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
229960003510 propiverine Drugs 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
231100000721 toxic potential Toxicity 0.000 description 1
230000007306 turnover Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/50—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Urology & Nephrology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)
Materials For Medical Uses (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO19975666A 1995-06-07 1997-12-05 Pyrrolderivater og medisinsk sammensetning NO321606B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP14069895		1995-06-07
PCT/JP1996/001526 WO1996040634A1 (fr)	1995-06-07	1996-06-06	Derives du pyrrole et composition medicamenteuse les renfermant

Publications (3)

Publication Number	Publication Date
NO975666D0 NO975666D0 (no)	1997-12-05
NO975666L NO975666L (no)	1998-02-09
NO321606B1 true NO321606B1 (no)	2006-06-12

Family

ID=15274666

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19975666A NO321606B1 (no)	1995-06-07	1997-12-05	Pyrrolderivater og medisinsk sammensetning

Country Status (20)

Country	Link
US (2)	US5998459A (ru)
EP (1)	EP0842923B1 (ru)
JP (1)	JP3160910B2 (ru)
KR (1)	KR100275222B1 (ru)
CN (2)	CN1090617C (ru)
AT (1)	ATE318799T1 (ru)
AU (1)	AU710683B2 (ru)
BR (1)	BR9608502A (ru)
CA (1)	CA2223918C (ru)
DE (1)	DE69635857T2 (ru)
DK (1)	DK0842923T3 (ru)
ES (1)	ES2259795T3 (ru)
HU (1)	HUP9802290A3 (ru)
MX (1)	MX9709475A (ru)
NO (1)	NO321606B1 (ru)
NZ (1)	NZ309151A (ru)
PT (1)	PT842923E (ru)
RU (1)	RU2166941C2 (ru)
TW (1)	TW504503B (ru)
WO (1)	WO1996040634A1 (ru)

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WO1999036068A1 (fr) *	1998-01-14	1999-07-22	Nippon Shinyaku Co., Ltd.	Activateurs des canaux de potassium
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KR20030019326A (ko) *	2000-03-21	2003-03-06	니뽄 신야쿠 가부시키가이샤	방출 제어형 경구 투여 제제
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TWI271402B (en) *	2002-10-15	2007-01-21	Tanabe Seiyaku Co	Large conductance calcium-activated K channel opener
JP4808154B2 (ja) *	2003-03-13	2011-11-02	バーテックスファーマシューティカルズインコーポレイテッド	プロテインキナーゼインヒビターとして有用な組成物
US20050075359A1 (en) *	2003-03-14	2005-04-07	Rikako Kono	Large conductance calcium-activated K channel opener
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JP2005325103A (ja) *	2004-04-13	2005-11-24	Tanabe Seiyaku Co Ltd	医薬組成物
WO2006130493A2 (en) *	2005-05-31	2006-12-07	Vertex Pharmaceuticals Incorporated	Heterocycles useful as modulators of ion channels
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PE20070341A1 (es) *	2005-07-29	2007-04-13	Wyeth Corp	Derivados de pirrol como moduladores del receptor de progesterona
TW200948362A (en)	2008-04-09	2009-12-01	Mitsubishi Tanabe Pharma Corp	New compounds and their uses
CN107207488B (zh)	2014-12-17	2020-11-17	伦敦皇家学院	作为视黄酸受体β(RARβ)激动剂的双环杂芳基-杂芳基-苯甲酸化合物
GB201610867D0 (en)	2016-06-22	2016-08-03	King's College London	Crystalline forms of a therapeutic compound and processes for their preparation

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FR2569189B1 (fr) *	1984-08-14	1986-12-19	Roussel Uclaf	Nouveaux derives du pyrrole, leur procede de preparation et leur application comme pesticides
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1996
- 1996-06-06 BR BR9608502A patent/BR9608502A/pt not_active Application Discontinuation
- 1996-06-06 WO PCT/JP1996/001526 patent/WO1996040634A1/ja active IP Right Grant
- 1996-06-06 PT PT96916319T patent/PT842923E/pt unknown
- 1996-06-06 JP JP50031097A patent/JP3160910B2/ja not_active Expired - Fee Related
- 1996-06-06 NZ NZ309151A patent/NZ309151A/xx not_active IP Right Cessation
- 1996-06-06 CN CN96194448A patent/CN1090617C/zh not_active Expired - Fee Related
- 1996-06-06 DE DE69635857T patent/DE69635857T2/de not_active Expired - Lifetime
- 1996-06-06 ES ES96916319T patent/ES2259795T3/es not_active Expired - Lifetime
- 1996-06-06 US US08/973,369 patent/US5998459A/en not_active Expired - Fee Related
- 1996-06-06 AU AU59109/96A patent/AU710683B2/en not_active Ceased
- 1996-06-06 CA CA002223918A patent/CA2223918C/en not_active Expired - Fee Related
- 1996-06-06 RU RU98100090/14A patent/RU2166941C2/ru not_active IP Right Cessation
- 1996-06-06 HU HU9802290A patent/HUP9802290A3/hu unknown
- 1996-06-06 AT AT96916319T patent/ATE318799T1/de not_active IP Right Cessation
- 1996-06-06 MX MX9709475A patent/MX9709475A/es not_active IP Right Cessation
- 1996-06-06 DK DK96916319T patent/DK0842923T3/da active
- 1996-06-06 KR KR1019970708809A patent/KR100275222B1/ko not_active IP Right Cessation
- 1996-06-06 EP EP96916319A patent/EP0842923B1/en not_active Expired - Lifetime
- 1996-06-18 TW TW085107349A patent/TW504503B/zh not_active IP Right Cessation
1997
- 1997-12-05 NO NO19975666A patent/NO321606B1/no unknown
1999
- 1999-07-30 US US09/365,096 patent/US6172102B1/en not_active Expired - Fee Related
2001
- 2001-10-15 CN CN01135586A patent/CN1349796A/zh active Pending

Also Published As

Publication number	Publication date
CN1186485A (zh)	1998-07-01
RU2166941C2 (ru)	2001-05-20
DK0842923T3 (da)	2006-06-19
PT842923E (pt)	2006-07-31
HUP9802290A3 (en)	2002-02-28
KR19990022329A (ko)	1999-03-25
KR100275222B1 (ko)	2001-02-01
CA2223918A1 (en)	1996-12-19
CN1349796A (zh)	2002-05-22
AU5910996A (en)	1996-12-30
US5998459A (en)	1999-12-07
NO975666D0 (no)	1997-12-05
BR9608502A (pt)	1999-07-06
CN1090617C (zh)	2002-09-11
US6172102B1 (en)	2001-01-09
EP0842923B1 (en)	2006-03-01
ES2259795T3 (es)	2006-10-16
TW504503B (en)	2002-10-01
MX9709475A (es)	1998-02-28
DE69635857D1 (de)	2006-04-27
EP0842923A1 (en)	1998-05-20
AU710683B2 (en)	1999-09-30
NZ309151A (en)	2000-01-28
EP0842923A4 (en)	1999-12-29
WO1996040634A1 (fr)	1996-12-19
CA2223918C (en)	2006-01-10
ATE318799T1 (de)	2006-03-15
JP3160910B2 (ja)	2001-04-25
DE69635857T2 (de)	2006-10-19
HUP9802290A2 (hu)	1999-10-28
NO975666L (no)	1998-02-09

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